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Synfacts 2008(3): 0276-0276  
DOI: 10.1055/s-2008-1042679
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Desymmetrization and Kinetic Resolution of 1,2-Diols

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
O. Onomura*, H. Arimoto, Y. Matsumura, Y. Demizu
Nagasaki University, Japan
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

Prior to this work only two examples of semi-catalytic asymmetric oxidation of 1,2-diols using chiral dioxiranes and hypervalent iodine had been reported (K. Jakka, C.-G. Zhao Org. Lett. 2006, 8, 3013; U. Ladziata et al. Tetrahedron Lett. 2006, 47, 6301). This paper reports the first truly catalytic asymmetric oxidation of 1,2-diols promoted by NBS in the presence of a copper catalyst. Desymmetrization of meso-hydrobenzoin gave the α-keto alcohol in moderate yield and ee. Additionally, kinetic resolution of diols 5 could be achieved to produce enantioenriched 1,2-diols in moderate yields and with low enantioselectivity.